CA2090967C - Water soluble camptothecin analogues, processes and methods - Google Patents

Water soluble camptothecin analogues, processes and methods Download PDF

Info

Publication number
CA2090967C
CA2090967C CA002090967A CA2090967A CA2090967C CA 2090967 C CA2090967 C CA 2090967C CA 002090967 A CA002090967 A CA 002090967A CA 2090967 A CA2090967 A CA 2090967A CA 2090967 C CA2090967 C CA 2090967C
Authority
CA
Canada
Prior art keywords
camptothecin
compound
formula
liquid
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA002090967A
Other languages
English (en)
French (fr)
Other versions
CA2090967A1 (en
Inventor
Joseph M. Fortunak
Jeffery L. Wood
Antonietta R. Mastrocola
Mark Mellinger
Patrick L. Burk
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SmithKline Beecham Corp
Original Assignee
SmithKline Beecham Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp
Publication of CA2090967A1 publication Critical patent/CA2090967A1/en
Application granted granted Critical
Publication of CA2090967C publication Critical patent/CA2090967C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Auxiliary Devices For And Details Of Packaging Control (AREA)
  • Fodder In General (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA002090967A 1990-09-28 1991-09-23 Water soluble camptothecin analogues, processes and methods Expired - Lifetime CA2090967C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US58964390A 1990-09-28 1990-09-28
US589,643 1990-09-28
PCT/US1991/006888 WO1992005785A1 (en) 1990-09-28 1991-09-23 Water soluble camptothecin analogues, processes and methods

Publications (2)

Publication Number Publication Date
CA2090967A1 CA2090967A1 (en) 1992-03-29
CA2090967C true CA2090967C (en) 2007-02-06

Family

ID=24358879

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002090967A Expired - Lifetime CA2090967C (en) 1990-09-28 1991-09-23 Water soluble camptothecin analogues, processes and methods

Country Status (24)

Country Link
US (1) US5734056A (enrdf_load_stackoverflow)
EP (1) EP0547165B1 (enrdf_load_stackoverflow)
JP (1) JP2848958B2 (enrdf_load_stackoverflow)
CN (1) CN1033509C (enrdf_load_stackoverflow)
AT (1) ATE186461T1 (enrdf_load_stackoverflow)
AU (1) AU664830B2 (enrdf_load_stackoverflow)
CA (1) CA2090967C (enrdf_load_stackoverflow)
CZ (1) CZ51593A3 (enrdf_load_stackoverflow)
DE (1) DE69131775T2 (enrdf_load_stackoverflow)
DK (1) DK0547165T3 (enrdf_load_stackoverflow)
ES (1) ES2137932T3 (enrdf_load_stackoverflow)
FI (1) FI931384A7 (enrdf_load_stackoverflow)
GR (1) GR3031823T3 (enrdf_load_stackoverflow)
HU (1) HUT70024A (enrdf_load_stackoverflow)
IE (1) IE913402A1 (enrdf_load_stackoverflow)
IL (1) IL99571A (enrdf_load_stackoverflow)
NO (1) NO931153D0 (enrdf_load_stackoverflow)
NZ (1) NZ239947A (enrdf_load_stackoverflow)
PT (1) PT99109B (enrdf_load_stackoverflow)
SI (1) SI9111599A (enrdf_load_stackoverflow)
SK (1) SK283693B6 (enrdf_load_stackoverflow)
WO (1) WO1992005785A1 (enrdf_load_stackoverflow)
YU (1) YU159991A (enrdf_load_stackoverflow)
ZA (1) ZA917748B (enrdf_load_stackoverflow)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP9300587A0 (en) * 1992-11-12 1995-05-05 Glaxo Inc Water soluble camptothecin derivatives.
US5527913A (en) * 1993-02-25 1996-06-18 The Stehlin Foundation For Cancer Research Methods for purifying camptothecin compounds
US5880131A (en) * 1993-10-20 1999-03-09 Enzon, Inc. High molecular weight polymer-based prodrugs
US5447936A (en) * 1993-12-22 1995-09-05 Bionumerik Pharmaceuticals, Inc. Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof
GB9402934D0 (en) * 1994-02-16 1994-04-06 Erba Carlo Spa Camptothecin derivatives and process for their preparation
KR960029336A (ko) * 1995-01-09 1996-08-17 김충환 캄토테신 유도체, 그의 제조 방법 및 이를 함유하는 항암제
US5726181A (en) * 1995-06-05 1998-03-10 Bionumerik Pharmaceuticals, Inc. Formulations and compositions of poorly water soluble camptothecin derivatives
JPH08333370A (ja) * 1995-06-08 1996-12-17 Kyorin Pharmaceut Co Ltd 水に可溶な新規フルオロエチルカンプトテシン誘導体、及びその製造方法
AU7732996A (en) * 1995-11-22 1997-06-11 Research Triangle Institute Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties
GB9601779D0 (en) * 1996-01-30 1996-04-03 Pharmacia Spa 9, 10 Disubstituted camptothecin derivatives
US5731316A (en) 1996-01-30 1998-03-24 The Stehlin Foundation For Cancer Research Derivatives of camptothecin and methods of treating cancer using these derivatives
US6407118B1 (en) 1996-01-30 2002-06-18 The Stehlin Foundation For Cancer Research Derivatives of camptothecin and methods of treating cancer using these derivatives
US6096336A (en) * 1996-01-30 2000-08-01 The Stehlin Foundation For Cancer Research Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs
US6043367A (en) * 1998-09-30 2000-03-28 Roffler; Steve Proactive antitumor compounds
US6352996B1 (en) 1999-08-03 2002-03-05 The Stehlin Foundation For Cancer Research Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs
US6228855B1 (en) 1999-08-03 2001-05-08 The Stehlin Foundation For Cancer Research Aromatic esters of camptothecins and methods to treat cancers
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
WO2004055020A1 (en) * 2002-12-16 2004-07-01 Council Of Scientific And Industrial Research Process for the direct preparation of 5-alkoxy and 5-acyloxy analogues of campthothecins or mappicene ketones
AU2003223109A1 (en) * 2003-03-31 2004-10-25 Council Of Scientific And Industrial Research Process for preparing topotecan from 10-hydroxy-4-(s) camptothecin
EP1628982B1 (en) 2003-05-12 2012-10-31 ScinoPharm Taiwan, Ltd. Process for the preparation of 7-alkyl-10-hydroxy-20(s)-camptothecin
CZ299329B6 (cs) * 2003-08-26 2008-06-18 Pliva-Lachema A.S. Zpusob výroby 7-ethyl-10-[ 4-(1-piperidino)-1-piperidino]karbonyloxykamptothecinu
CZ298934B6 (cs) * 2003-08-26 2008-03-12 Pliva- Lachema A.S. Zpusob výroby 7-ethyl-10-hydroxykamptothecinu
TWI333492B (en) * 2003-11-12 2010-11-21 Smithkline Beecham Cork Ltd Crystalline topotecan hydrochloride product and preparation thereof
CZ299593B6 (cs) * 2003-12-16 2008-09-10 Pliva-Lachema A. S. Zpusob výroby 7-ethyl-10-hydroxykamptothecinu
US20050267141A1 (en) 2004-05-28 2005-12-01 Phytogen Life Sciences Inc. Process to prepare camptothecin derivatives
US20050272757A1 (en) * 2004-06-04 2005-12-08 Phytogen Life Sciences Inc. Process to prepare camptothecin derivatives and novel intermediate and compounds thereof
WO2006016203A1 (en) * 2004-08-09 2006-02-16 Shilpa Medicare Limited An improved process for the preparation of irinotecan hydrochloride trihydrate
MX2007005293A (es) * 2004-11-05 2007-07-19 Samyang Corp Formulacion farmaceutica para incrementar la solubilidad de compuestos de 10-hidroxicamptotecina en solventes polares no acuosos.
US20060135546A1 (en) * 2004-12-16 2006-06-22 Jagadevappa Basavaraja Methods for the purification of 20(S)- camptothecin
BRPI0613783A2 (pt) * 2005-07-18 2011-02-01 Bipar Sciences Inc tratamento de cáncer
KR20080068052A (ko) * 2005-10-10 2008-07-22 씨아이피엘에이 엘티디. 신규의 결정형
US7547785B2 (en) 2005-12-26 2009-06-16 Dr. Reddy's Laboratories Limited Process for preparing topotecan
WO2007127839A2 (en) * 2006-04-26 2007-11-08 The Regents Of The University Of California Compositions and methods for convection enhanced delivery of high molecular weight neurotherapeutics
AR060635A1 (es) 2006-04-27 2008-07-02 Banyu Pharma Co Ltd Derivados de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona, composiciones farmaceuticas que los comprenden y su uso en el tratamiento del cancer
US20100279327A1 (en) * 2006-06-12 2010-11-04 Bipar Sciences, Inc. Method of treating diseases with parp inhibitors
WO2008147418A1 (en) * 2006-06-12 2008-12-04 Bipar Sciences, Inc. Method of treating diseases with parp inhibitors
US20080039485A1 (en) * 2006-08-08 2008-02-14 Targetgen Biotechnology Co., Ltd. Low-dose-long-term pharmaceutical composition comprising camptothecin derivatives for the treatment of cancers
JP2008081492A (ja) 2006-08-31 2008-04-10 Banyu Pharmaceut Co Ltd オーロラａ選択的阻害作用を有する新規アミノピリジン誘導体
AU2007292387A1 (en) * 2006-09-05 2008-03-13 Bipar Sciences, Inc. Treatment of cancer
AU2007292306A1 (en) * 2006-09-05 2008-03-13 Bipar Sciences, Inc. Inhibition of fatty acid synthesis by PARP inhibitors and methods of treatment thereof
US7977336B2 (en) 2006-12-28 2011-07-12 Banyu Pharmaceutical Co. Ltd Aminopyrimidine derivatives as PLK1 inhibitors
US7977483B2 (en) 2007-04-11 2011-07-12 Scinopharm Taiwan, Ltd. Process for making topotecan
CN101903025A (zh) * 2007-10-19 2010-12-01 彼帕科学公司 利用苯并吡喃酮-型parp抑制剂治疗癌症的方法和组合物
AU2008315048A1 (en) 2007-10-23 2009-04-30 Msd K.K. Pyridone-substituted-dihydropyrazolopyrimidinone derivative
CN101918003A (zh) * 2007-11-12 2010-12-15 彼帕科学公司 单独使用parp抑制剂或与抗肿瘤剂组合治疗子宫癌和卵巢癌
EP2217227B1 (en) * 2007-11-12 2013-08-21 BiPar Sciences, Inc. Treatment of breast cancer with 4-iodo-3-nitrobenzamide in combination with anti-tumor agents
ITMI20072268A1 (it) 2007-12-04 2009-06-05 Antibioticos Spa Polimorfi cristallini di topotecan cloridrato con elevato grado di purezza e metodi per la loro preparazione
CN101450949B (zh) * 2007-12-07 2011-10-05 上海龙翔生物医药开发有限公司 一种10-羟基喜树碱的化学半合成工艺
WO2009073869A1 (en) * 2007-12-07 2009-06-11 Bipar Sciences, Inc. Treatment of cancer with combinations of topoisomerase inhibitors and parp inhibitors
AU2009252303B2 (en) 2008-05-29 2013-04-04 Microbiopharm Japan Co., Ltd. Production method for camptothecin derivative
AU2010218781A1 (en) 2009-02-25 2011-07-28 Msd K.K. Pyrimidopyrimidoindazole derivative
EP2403339B1 (en) 2009-03-06 2017-01-18 Merck Sharp & Dohme Corp. Combination cancer therapy with an akt inhibitor and other anticancer agents
US8709420B2 (en) 2010-12-17 2014-04-29 Glaxosmithkline Intellectual Property Limited Pharmaceutical combination of pazopanib and topotecan to treat neuroblastoma, osteosarcoma, and rhabdomyosarcoma in a human
US20130303560A1 (en) 2011-02-01 2013-11-14 Sunnybrook Research Institute Combination
CN103145720B (zh) * 2013-02-20 2015-09-30 上海北卡医药技术有限公司 一种10-羟基喜树碱的一水合物的制备方法
EP2881396A1 (en) * 2013-12-03 2015-06-10 Synbias Pharma AG Method for the synthesis of irinotecan
AU2021226341A1 (en) 2020-02-25 2022-09-29 Mediboston Limited Camptothecin derivatives and conjugates thereof
WO2023220641A2 (en) 2022-05-11 2023-11-16 Juno Therapeutics, Inc. Methods and uses related to t cell therapy and production of same

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5842192B2 (ja) * 1974-05-18 1983-09-17 フセソユ−ズヌイ ナウチノ イスレドワ−チエレスキ− ヒミコ フアルマツエフチチエスキ− インスチツ−ト イメ−ニ エス オルジヨニキ−ゼ ５− オキシ −６− アミノメチルベンゾフランノ ユウドウタイノ セイホウ
US4473692A (en) * 1981-09-04 1984-09-25 Kabushiki Kaisha Yakult Honsha Camptothecin derivatives and process for preparing same
JPS595188A (ja) * 1982-06-30 1984-01-12 Yakult Honsha Co Ltd １０−ヒドロキシカンプトテシンの製造法
JPS5946284A (ja) * 1982-09-10 1984-03-15 Yakult Honsha Co Ltd １１−ニトロカンプトテシン誘導体およびその製造法
US4981968A (en) * 1987-03-31 1991-01-01 Research Triangle Institute Synthesis of camptothecin and analogs thereof
US4894456A (en) * 1987-03-31 1990-01-16 Research Triangle Institute Synthesis of camptothecin and analogs thereof
US4943579A (en) * 1987-10-06 1990-07-24 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Water soluble prodrugs of camptothecin
US5004758A (en) * 1987-12-01 1991-04-02 Smithkline Beecham Corporation Water soluble camptothecin analogs useful for inhibiting the growth of animal tumor cells
JPH0615547B2 (ja) * 1988-01-20 1994-03-02 株式会社ヤクルト本社 新規なカンプトテシン誘導体
GB9008605D0 (en) * 1990-04-17 1990-06-13 Smith Kline French Lab Process
HU213136B (en) * 1990-08-14 1997-02-28 Kyorin Seiyaku Kk Process for producing fluoroethyl camptothecin derivatives and pharmaceutical compositions containing them
US5352789A (en) * 1993-02-25 1994-10-04 The Stehlin Foundation For Cancer Research Methods for purifying camptothecin compounds

Also Published As

Publication number Publication date
FI931384L (fi) 1993-03-26
US5734056A (en) 1998-03-31
ZA917748B (en) 1992-09-30
CA2090967A1 (en) 1992-03-29
GR3031823T3 (en) 2000-02-29
SK25993A3 (en) 1993-07-07
SK283693B6 (sk) 2003-12-02
IL99571A0 (en) 1992-08-18
EP0547165A4 (enrdf_load_stackoverflow) 1994-03-30
PT99109B (pt) 1999-02-26
ATE186461T1 (de) 1999-11-15
AU664830B2 (en) 1995-12-07
NZ239947A (en) 1994-07-26
JPH06501476A (ja) 1994-02-17
PT99109A (pt) 1992-08-31
NO931153L (no) 1993-03-26
IL99571A (en) 2000-08-31
JP2848958B2 (ja) 1999-01-20
IE913402A1 (en) 1992-04-08
FI931384A0 (fi) 1993-03-26
YU159991A (sh) 1994-06-10
ES2137932T3 (es) 2000-01-01
EP0547165A1 (en) 1993-06-23
CN1033509C (zh) 1996-12-11
DE69131775T2 (de) 2000-04-20
AU8739991A (en) 1992-04-28
FI931384A7 (fi) 1993-03-26
DE69131775D1 (de) 1999-12-16
HU9300878D0 (en) 1993-06-28
CZ51593A3 (en) 1994-01-19
WO1992005785A1 (en) 1992-04-16
SI9111599A (sl) 1998-02-28
NO931153D0 (no) 1993-03-26
HUT70024A (en) 1995-09-28
CN1062731A (zh) 1992-07-15
DK0547165T3 (da) 2000-03-27
EP0547165B1 (en) 1999-11-10
HK1012283A1 (en) 1999-07-30

Similar Documents

Publication Publication Date Title
CA2090967C (en) Water soluble camptothecin analogues, processes and methods
KR100191193B1 (ko) 6환 화합물
US5049668A (en) 10,11-methylenedioxy-20(RS)-camptothecin analogs
US5180722A (en) 10,11-methylenedioxy-20(RS)-camptothecin and 10,11-methylenedioxy-20(S)-camptothecin analogs
EP0694035B1 (en) Water-soluble camptothecin derivatives, process for their preparation and their use as antitumor agents
NZ235329A (en) 20(s or rs)-camptothecin derivatives and pharmaceutical compositions
US5340817A (en) Method of treating tumors with anti-tumor effective camptothecin compounds
AU8940491A (en) Substituted indolizino(1,2-b)quinolinones
JPH0372228B2 (enrdf_load_stackoverflow)
US5840899A (en) Method for the preparation of 9-amino camptothecin
EP0824534B1 (en) 9,10 disubstituted camptothecin derivatives with antitumor activity
HK1012283B (en) Process for the preparation of water-soluble camptothecin analogues, as well as the compounds 10-hydroxy-11-c(1-6)-alkoxycamptothecin
CA2493090C (fr) Nouveaux derives de benzo[b]chromeno-naphthyridin-7-one et de pyrano[2'3':7,8]quino[2,3-b]quinoxalin-7-one, leur procede de preparation et les compositions pharmaceutiques qui lescontiennent
JPH07101956A (ja) ヒドロキシカンプトテシン化合物の製法
KR19990036194A (ko) 신규한 20(ｓ)-캄프토덱신의 수용성 ｃ-고리 동족체
US6476225B2 (en) Process for purifying 20(S)-camptothecin
IT202300003888A1 (it) Processo di preparazione di un farmaco usato per trattare la dipendenza da nicotina
CN101432288B (zh) 喜树碱衍生物的制造方法
AU6340490A (en) 10,11-methylenedioxy-20(rs)-camptothecin and 10,11-methylenedioxy-20(s)-camptothecin analogs

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry